1. Technical Field of the Invention
This invention relates to secondary alkyl amine derivatives of ethylenediamine. More particularly, this invention relates to secondary alkyl amine derivatives of ethylenediamine prepared by the reaction of ethylenediamine with a methyl alkyl ketone in the presence of hydrogen and a hydrogenation catalyst. Still more particularly, this invention relates to a continuous method utilizing a methyl alkyl ketone wherein the alkyl group contains 1 to 4 carbon atoms wherein ethylenediamine is continuously reacted with the methyl alkyl ketone in the presence of hydrogen and a hydrogenation catalyst to provide secondary alkyl amine derivatives of ethylenediamine.
2. Prior Art
Speranza et al. U.S. Pat. No. 3,110,732 is directed to a method for preparing primary amine derivatives of polyoxyalkylene glycol by a three-step process wherein an alkanolamine having a primary amine group is reacted with a higher carbonyl compound such as methylethyl ketone, isobutyraldehyde, etc., to form a condensation product which may be either a Schiff base or an oxazolidine which is thereafter alkoxylated with an alkylene oxide to provide an adduct followed by hydrolysis of the adduct to form a primary amine basic polyether composition.
Speranza U.S. Pat. No. 3,364,239 is directed to secondary amino polyalkoxy monoalkanols which are prepared by reacting a primary amino polyalkoxy alkanol with a higher carbonyl compound such as methylethyl ketone, butyraldehyde, etc., to form a Schiff base reaction product which is thereafter hydrogenated in the presence of a hydrogenation catalyst at an elevated temperature and pressure to provide the secondary amino polyalkoxy monoalkanol. The reference contains an example III wherein acetone was reacted in an autoclave with aminoethoxyethanol in the presence of hydrogen and a hydrogenation catalyst to provide a reaction product comprising N-isopropylaminoethoxyethanol.
Malz, Jr. et al. U.S. Pat. No. 4,607,104 is directed to a process wherein 2,2,6,6-tetraalkyl-4-piperidylamines are prepared by reacting an amine with 2,2,6,6-tetraalkyl-4-piperidone in the presence of water, an aliphatic alcohol or aliphatic glycol and a platinum, nickel or cobalt catalyst.